The Hidden Cost of "Making It Work" in School Operations

Most district operations aren't broken. They're held together by a few people who know every workaround, by scripts and spreadsheets nobody else understands, and by teams so good at filling gaps that no one sees the effort.  

In this episode of Conversations with Educators, hosts Max Gregory and Dr. Ros Jackson sat down with Dr. Jessica Preisig, Assistant Superintendent for Technology Services at the School District of Pickens County in South Carolina, to talk about what "good enough" really costs and what it takes to build vendor relationships worth trusting.

Key Takeaways from the Session

• When a team gets really good at making things work, the effort becomes invisible, and the rest of the district stops realizing how complex its asks really are.
• A workaround starts as smart problem solving. The trouble comes when it quietly becomes the workflow, and you usually only find out when the person who runs it moves on.
• Knowledge that lives in one person is organizational risk. Pairing experts with colleagues on purpose, and documenting in shared spaces, spreads that knowledge before it's needed.
• The true cost of a breakdown isn't the help ticket. It's lost instructional time, delayed work, and, most of all, eroded trust that takes far longer to rebuild than the system does.
• "Does it work?" is a low bar. Districts should be asking whether a tool delivers value, protects data, meets accessibility needs, and fits the ecosystem they've already invested in.
• Fast, honest communication from district tech teams and from vendors buys grace, builds trust, and gives everyone time to solve the actual problem.

What does "making it work" actually look like day to day in your district?

Preisig: I think most people in my district, especially our classroom teachers, would be surprised by it. There's a feeling that everything is magical and automated, that systems just talk to each other with ease. In reality, a lot of our daily work involves connecting systems, processes, and people that weren't designed to be that smooth.

That's especially true for systems that take in employee data. The edtech world has done a lot of work to build great ecosystems for students and make student logins and data transfers relatively seamless. When it comes to the adults in the building, it can be a real challenge.

My team has gotten really good at filling in the gaps, and that's part of the challenge. Sometimes we get so good at making things work that we normalize or hide the effort it takes. I always tell my team, people don't realize what they're asking. They don't know the complexity of the ask, because from the school's side it looks like you push a button and magic happens.

I recently saw a meme that said every district has a Carol, that one person who knows all things. Ours is Brenda. Every district is lucky to have one, until the day that person isn’t there.

When does a workaround become permanent infrastructure?

Preisig: I don't know if it happens in a moment or just over time. In K-12, we have so many systems that depend on student, staff, course, and enrollment data being accurate and available at all times, very quickly. So, we've found a lot of solutions that make things work. Sometimes it's a manual export and import, sometimes a reconciliation process, sometimes one of our team members writes a script.

It's usually not until the person who runs that process changes roles that you realize, oh, that's where the problem is. Building those manual processes starts as problem solving. We want to get people what they need as quickly as possible. But at some point, the workaround becomes the workflow, and that's when it's time to start asking harder questions.

We've been working through that as a district with something as simple as badge access. When you try to automate for efficiency, you run into hurdles. Somebody's role may not actually require access to a certain space, and you have to negotiate all of those details along the way.

Why can "customization" make things harder?

Preisig: Solution providers will sometimes throw out words like customization. To our academic services, finance, or HR departments, that sounds great. But if you're the person who understands the system, you know that every customization isn't necessarily part of the core workflow. The more something gets customized, the harder it is to automate and to build reliable processes around it.

What's a process in your district that only one or two people understand end to end?

Preisig: The complexity surrounding our student information system and all the processes that depend on it. From start to finish, I'd say one or two people really understand it. It's not just knowing the SIS. It's understanding everything that happens downstream when you go to troubleshoot. When something changes in the SIS, or even in our HR platform, it can affect access, just because somebody made a typo.

Understanding how enrollment changes, what needs to sync, what happens when a sync doesn't occur, and how many times a day each of our 160-plus applications pulls in student data. That's the piece very few people fully grasp.

Before COVID, we had great processes in place, but they all centered on one person. When that person was out for a while, we realized what a big risk that was. One person can't be the keeper of all the information. That happened just as I was moving into my role, so one of the things we did across our whole department was focus on teams.

When Brenda came back to us, she spent a lot of time pouring into other people. We intentionally paired her with two colleagues in the department. Not because she's going anywhere, but because we want that knowledge built across teams instead of living with one person.

As a leader, that's part of my responsibility: building cross-functional teams, making sure information is shared responsibly, and creating the time and structures for that sharing to actually happen. It's easy to shoot off an email to one person and say, "Can you fix this for us?" But what happens long term is important to think about up front. Our greatest strength is our people, and that's also our greatest vulnerability when it comes to technology and systems.

How do you get that knowledge out of people's heads and onto paper?

Preisig: We're building out a knowledge base across our teams. They work together and then get things down on paper as much as possible. Luckily, Brenda has kept great notes over the years, and our other teams do that too. As people come and go, the key is making sure that information isn't living in someone's personal drive. It needs to be in a shared drive, part of a team.

What I've found is that part of that training is making sure people know what questions to ask. Knowing the right questions up front matters more than finding the answer on a sheet.

What's the real cost when something finally breaks?

Preisig: I think we underestimate the cost because we only measure the immediate technical problem, the one ticket that gets opened and closed. There's the time our tech team spends investigating and resolving it, but that's just the beginning.  

There's the teacher who has to change her instructional plan. The student who loses access to a learning experience in the moment. The school leader fielding questions from everybody asking whether something's broken. And all the other work that gets delayed because everyone shifts from what they had planned for the day to firefighting.

If an issue involves multiple vendors, that adds another layer. Some of our most complex problems aren't between us and one solution provider, they're between solution providers. Someone in our district usually ends up coordinating that investigation and communicating across everyone, and it's hard to get everybody in the same room. Even though we didn't build the products, we're often the ones finding the solution.

When that happens, especially when it takes time, the greatest cost in our department is trust. Every time something doesn't work as expected, we lose a little confidence from the people we're asking to use that tool. Over time, teachers become hesitant to build technology into their lessons, and school leaders start asking whether it's the right solution at all. With today's conversations around screen time, we really don't want to erode that trust.

Trust takes a long time to build, and it can be gone in a flash. We might resolve a technical issue in a matter of hours, but an hour in a classroom is a really long time. You can restore a system, but it takes a lot longer to restore someone's confidence in it.

When did "good enough" stop being good enough?

Preisig: There was a time when we were satisfied if we could get a product implemented and get students and teachers connected and using it. Today, that's a pretty low bar. As our technology ecosystem and its complexity have grown, we need to ask bigger questions.  

• Is the tool actually delivering value for our students?
• Does it protect student data and privacy?
• Can it exchange information with the other systems we've invested in, and how much effort does that take from our team?

That's one of the reasons I've become so involved in conversations around interoperability, standards, and building a trusted ecosystem. I serve on the board of 1EdTech, transitioning from K-12 to the overall membership board. We need to move beyond asking whether something works and start asking whether it fits the broader ecosystem we're building, and whether it checks all the boxes on data privacy, security, and accessibility. For solution providers, knowing how your platform fits into that larger ecosystem is just as important as knowing what it's built to do.

What does a real partnership between districts and vendors look like?

Preisig: Districts should be partners not just in the transaction of buying, but in shaping the solution. Too often we're left figuring out how to make everything fit together after we've already purchased something. There's room for pilots where we can say, "Here's what we need as a K-12 district to make this work in our environment," and find out whether a solution provider can make that happen. Just because we can make something work doesn't mean we should have to.

We have 16,000 students and more than 2,000 employees, and I have 20 people on my team. With a team that lean, it's really important that our platforms and solution providers work well together.

It takes work on both sides. Not every district is willing to give its time and energy to building a better solution, but I think that's time well invested, and the same is true for vendors. I've had the chance to speak at national conferences about partner relationships, and the core idea is that it takes both sides to move beyond something transactional. When that works well, you build trust as colleagues, and it levels the playing field because everyone recognizes they're partners in the work.

What should vendors do when something goes wrong?

Preisig: When solution providers are upfront about an issue, it makes things so much easier on us. Sometimes there's a hesitancy to claim ownership, where people would rather wait and say, "I don't know if that's on our end or your end." The sooner someone knows about an issue and communicates it, the better.

I spent over a decade in the classroom, and when you're inside those four walls, you just want to know: is it just me, or is it everybody? If it's everybody, there's some comfort in that. Somebody's working on it, and I can keep rolling. If it's just me, I need to handle it differently. I feel the same way as a district.

That communication piece is a huge part of building trust, and it's what my team is focused on this year. Our high-impact word is trust, not just between our department and the people we serve, but within our department too, taking care of the trust we have with each other.

Final Thoughts

The work that holds a district together is often the work nobody sees, and that invisibility is exactly what makes it risky. Preisig's answer isn't to stop making things work. It's to share knowledge on purpose, communicate early, and expect more from the tools and partners a lean team depends on. Systems can be restored in hours. Trust takes longer, which is why it's worth protecting first.

Make Test Season Less Dependent on Workarounds

Testing coordination is one of the places "making it work" hides best: the accommodations spreadsheet, the manual rosters, the one coordinator who knows how it all fits together.  

See how TestHound brings it into one place, or book a demo to talk through what test season looks like in your district.